Fungicides are compounds, of natural or synthetic origin, which act to protect and/or cure plants against damage caused by agriculturally relevant fungi. Generally, no single fungicide is useful in all situations. Consequently, research is ongoing to produce fungicides that may have better performance, are easier to use, and cost less.
The present disclosure relates to metalloenzyme inhibitors and their use as fungicides. The compounds of the present disclosure may offer protection against ascomycetes, basidiomycetes, deuteromycetes and oomycetes.
One embodiment of the present disclosure may include compounds of Formula I:

Where:
Z is optionally substituted 5-pyrimidinyl, optionally substituted 4-pyrimidinyl, optionally substituted thiazolyl, optionally substituted oxazolyl, optionally substituted 3-pyridinyl, or optionally substituted 4-pyridinyl;
n is 0 or 1;
R1 is alkyl, haloalkyl, aryl, or heteroaryl, each optionally substituted with 0, 1, 2 or 3 independent R4;
R2 is aryl, heteroaryl aryloxy, heteroaryloxy, arylalkynyl, heteroarylalkynyl, arylalkyl, heteroarylalkyl, arylalkoxy, heteroarylalkoxy, aryloxyalkyl, or heteroaryloxyalkyl wherein each aryl or heteroaryl is optionally substituted with 0, 1, 2 or 3 independent R4;
R3 is independently H, alkyl, aryl, substituted aryl, heteroaryl, arylalkyl, or heteroarylalkyl, —C(O)alkyl, —C(O)aryl, —Si(alkyl)3, each optionally substituted with 0, 1, 2 or 3 independent R4;
R4 is independently aryl, heteroaryl, alkyl, thioalkyl, cyano, cyanoalkyl, haloalkyl, hydroxy, alkoxy, halo, haloalkoxy, —C(O)alkyl, —C(O)OH, —C(O)Oalkyl, —SCF3, —SF5, —SCN, or SO2(alkyl); and
R5-R7 are independently selected from the group consisting of H, alkyl, alkoxy, halo, and haloalkyl;
With the proviso that when n=1, Z is 1-tetrazolyl or 5-pyrimidinyl.
Another embodiment of the present disclosure may include a fungicidal composition for the control or prevention of fungal attack comprising the compounds described above and a phytologically acceptable carrier material.
Yet another embodiment of the present disclosure may include a method for the control or prevention of fungal attack on a plant, the method including the steps of applying a fungicidally effective amount of one or more of the compounds described above to at least one of the fungus, the plant, and an area adjacent to the plant.
It will be understood by those skilled in the art that the following terms may include generic “R”-groups within their definitions, e.g., “the term alkoxy refers to an —OR substituent”. It is also understood that within the definitions for the following terms, these “R” groups are included for illustration purposes and should not be construed as limiting or being limited by substitutions about Formula I.
The term “alkyl” refers to a branched, unbranched, or saturated cyclic carbon chain, including, but not limited to, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tertiary butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
The term “alkenyl” refers to a branched, unbranched or cyclic carbon chain containing one or more double bonds including, but not limited to, ethenyl, propenyl, butenyl, isopropenyl, isobutenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and the like.
The term “alkynyl” refers to a branched or unbranched carbon chain containing one or more triple bonds including, but not limited to, propynyl, butynyl and the like.
The term “aryl” or “Ar” refers to any aromatic ring, mono- or bi-cyclic, containing 0 heteroatoms.
The term “heterocycle” refers to any aromatic or non-aromatic ring, mono- or bi-cyclic, containing one or more heteroatoms.
The term “heteroaryl” or “Het” refers to any aromatic ring, mono- or bi-cyclic, containing one or more heteroatoms.
The term “alkoxy” refers to an —OR substituent.
The term “aryloxy” refers to an —OAr substituent.
The term “hetaryloxy” refers to an —OHet substituent.
The term “arylalkynyl” refers to an Ar substituent.
The term “heteroarylalkynyl” refers to an Het substituent.
The term “cyano” refers to a —C≡N substituent.
The term “hydroxyl” refers to an —OH substituent.
The term “amino” refers to a —NR2 substituent.
The term “arylalkyl” refers to an -alkyl-Ar substituent.
The term “heteroarylalkyl” refers to an -alkyl-Het substituent.
The term “arylalkoxy” refers to —O(CH2)nAr where n is an integer selected from the list 1, 2, 3, 4, 5, or 6.
The term “heteroarylalkoxy” refers to —O(CH2)nHet where n is an integer selected from the list 1, 2, 3, 4, 5, or 6.2
The term “haloalkoxy” refers to an —OR substituent, wherein R is substituted with Cl, F, Br, or I, or any combination of one or more halogen atoms.
The term “haloalkyl” refers to an alkyl, which is substituted with one or more halogen atoms.
The term “cyanoalkyl” refers to an alkyl, which is substituted with a cyano group.
The term “halogen” or “halo” refers to one or more halogen atoms, defined as F, Cl, Br, and I.
The term “nitro” refers to a —NO2 substituent.
The term thioalkyl refers to an —SR substituent.
Throughout the disclosure, reference to the compounds of Formula I is read as also including diastereomers, enantiomers, and mixtures thereof. In another embodiment, Formula I is read as also including salts or hydrates thereof. Exemplary salts include, but are not limited to: hydrochloride, hydrobromide, and hydroiodide.
It is also understood by those skilled in the art that additional substitution is allowable, unless otherwise noted, as long as the rules of chemical bonding and strain energy are satisfied and the product still exhibits fungicidal activity.
Another embodiment of the present disclosure is a use of a compound of Formula I, for protection of a plant against attack by a phytopathogenic organism or the treatment of a plant infested by a phytopathogenic organism, comprising the application of a compound of Formula I, or a composition comprising the compound to soil, a plant, a part of a plant, foliage, seeds, and/or roots.
Additionally, another embodiment of the present disclosure is a composition useful for protecting a plant against attack by a phytopathogenic organism and/or treatment of a plant infested by a phytopathogenic organism comprising a compound of Formula I and a phytologically acceptable carrier material.